Plants of the Amaryllidaceae family are promising therapeutic tools for human diseases and have been used as alternative medicines. The specific secondary metabolites of this plant family, called Amaryllidaceae alkaloids (AA), have attracted considerable attention due to their interesting pharmacological activities. One of them, galantamine, is already used in the therapy of Alzheimer's disease as a long acting, selective, reversible inhibitor of acetylcholinesterase. One group of AA is the montanine-type, such as montanine, pancracine and others, which share a 5,11-methanomorphanthridine core. So far, only 14 montanine-type alkaloids have been isolated. Compared with other structural-types of AA, montanine-type alkaloids are predominantly present in plants in low concentrations, but some of them display promising biological properties, especially in vitro cytotoxic activity against different cancerous cell lines. The present review aims to summarize comprehensively the research that has been published on the Amaryllidaceae alkaloids of montanine-type.
- MeSH
- alkaloidy amarylkovitých chemie izolace a purifikace farmakologie MeSH
- Amaryllidaceae chemie metabolismus MeSH
- antiprotozoální látky chemie izolace a purifikace farmakologie MeSH
- cholinesterasové inhibitory chemie izolace a purifikace farmakologie MeSH
- fenantridiny chemie izolace a purifikace farmakologie MeSH
- fytogenní protinádorové látky chemie izolace a purifikace farmakologie MeSH
- galantamin chemie izolace a purifikace farmakologie MeSH
- heterocyklické sloučeniny tetra- a více cyklické chemie izolace a purifikace farmakologie MeSH
- inhibiční koncentrace 50 MeSH
- isochinoliny chemie izolace a purifikace farmakologie MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- nootropní látky chemie izolace a purifikace farmakologie MeSH
- rostlinné extrakty chemie MeSH
- sekundární metabolismus MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- přehledy MeSH
Scadoxus puniceus (Amaryllidaceae), a medicinal plant of high value in South Africa, is used as a component of a traditional herbal tonic prescribed to treat several ailments. Ultra-high performance liquid chromatography-tandem mass spectrometry quantified the phenolic compounds in different organs of S. puniceus. Gravity column chromatography was used to separate fractions and active compounds. The structure of these compounds was determined using 1D and 2D nuclear magnetic resonance and mass spectroscopic techniques. A microplate technique was used to determine the acetylcholinesterase inhibitory activity of the pure compounds. Metabolite profiling revealed a greater profusion of hydroxycinnamic acids (69.5%), as opposed to hydroxybenzoic acids (30.5%). Chlorogenic acid was the most abundant (49.6% of hydroxycinnamic acids) compound. In addition to chlorogenic acid, the study is the first to report the presence of sinapic, gallic, and m-hydroxybenzoic acids in the Amaryllidaceae. Chromatographic separation of S. puniceus led to the isolation of haemanthamine (1), haemanthidine (2), and a rare chlorinated amide, metolachlor (3), the natural occurrence of which is described for the first time. Haemanthamine, haemanthidine, and metolachlor displayed strong acetylcholinesterase inhibitory activity (IC50 ; 23.1, 23.7, and 11.5 μM, respectively). These results substantiate the frequent use of S. puniceus as a medicinal plant and hold much promise for further pharmaceutical development.
- MeSH
- acetamidy chemie izolace a purifikace metabolismus farmakologie MeSH
- alkaloidy amarylkovitých chemie izolace a purifikace metabolismus farmakologie MeSH
- Amaryllidaceae chemie metabolismus MeSH
- cholinesterasové inhibitory chemie izolace a purifikace farmakologie MeSH
- fenantridiny chemie izolace a purifikace metabolismus farmakologie MeSH
- kyseliny kumarové chemie izolace a purifikace metabolismus farmakologie MeSH
- léčivé rostliny chemie MeSH
- rostlinné extrakty chemie izolace a purifikace metabolismus farmakologie MeSH
- tandemová hmotnostní spektrometrie MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Jihoafrická republika MeSH
In this study, the South African Amaryllid Boophone haemanthoides was examined for its phytochemical composition and cytotoxicity. In the process eight alkaloid structures, including the new compound distichaminol, were identified in bulb ethanolic extracts. Of the isolates, lycorine and distichamine exhibited strong activities against human acute lymphoblastic leukemia (CEM), breast adenocarcinoma (MCF7) and cervical adenocarcinoma (HeLa) cells with IC50S ranging from 1.8 to 9.2 microM.
- MeSH
- alkaloidy amarylkovitých chemie izolace a purifikace MeSH
- fenantridiny izolace a purifikace MeSH
- fytogenní protinádorové látky chemie izolace a purifikace MeSH
- HeLa buňky MeSH
- lidé MeSH
- liliovité chemie MeSH
- MFC-7 buňky MeSH
- molekulární struktura MeSH
- screeningové testy protinádorových léčiv MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
The content of the seven quaternary benzo[c]phenanthridine alkaloids (QBA) sanguinarine (SA), chelerythrine (CHE), chelirubine (CHR), chelilutine (CHL), sanguilutine (SL), sanguirubine (SR) and macarpine (MA) was determined in the underground part of six plant species of the family Papaveraceae (Sanguinaria canadensis L., Dicranostigma lactucoides HOOK.f.et THOMS, Chelidonium majus L., Macleaya cordata (Willd.), Macleaya microcarpa (Maxim) and Stylophorum lasiocarpum (Oliv.)). HPLC method with reversed phase column Synergi Max-RP C-12 Phenomenex was used, mobile phase consisted of heptanesulfonic acid (0.01 mol/l) with triethanolamine (0.1 mol/l) in redistilled water, pH 2.5, acetonitrile gradient 25-60% during 25 min. Detection was performed at 280 nm. The highest content of SA and CHE was found in the roots of D. lactucoides (1.99%, resp. 3.43% of the dried roots). In rhizomes of S. canadensis was their content more then two times lower.
- MeSH
- acetonitrily chemie MeSH
- alkaloidy analýza chemie MeSH
- druhová specificita MeSH
- ethanolaminy chemie MeSH
- fenantridiny analýza chemie izolace a purifikace MeSH
- financování organizované MeSH
- kalibrace MeSH
- koncentrace vodíkových iontů MeSH
- kořeny rostlin chemie MeSH
- léčivé rostliny anatomie a histologie chemie MeSH
- methanol chemie MeSH
- molekulární struktura MeSH
- Papaveraceae anatomie a histologie chemie MeSH
- regresní analýza MeSH
- reprodukovatelnost výsledků MeSH
- rostlinné extrakty chemie MeSH
- spektrofotometrie ultrafialová MeSH
- voda chemie MeSH
- vysokoúčinná kapalinová chromatografie metody přístrojové vybavení MeSH
- Klíčová slova
- nuciferin, mecambridin, isothebain, orientalidin, oxysanguinarin, koptisin, salutaridin,
- MeSH
- alkaloidy izolace a purifikace MeSH
- apomorfin analogy a deriváty izolace a purifikace MeSH
- aporfiny izolace a purifikace MeSH
- berberin analogy a deriváty izolace a purifikace MeSH
- chinoliziny izolace a purifikace MeSH
- chromatografie na tenké vrstvě MeSH
- fenantridiny izolace a purifikace MeSH
- morfinany izolace a purifikace MeSH
- Papaver chemie MeSH
- thebain izolace a purifikace MeSH
